


Last Chance at a First Time

by lucifers_first



Category: Supernatural
Genre: M/M
Language: English
Status: Completed
Published: 2014-11-29
Updated: 2014-11-29
Packaged: 2018-02-27 10:31:09
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,959
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2689520
Author URL: https://archiveofourown.org/users/lucifers_first/pseuds/lucifers_first
Summary: <blockquote class="userstuff">
              <p>WINCEST. Seriously, don't like, don't read. Do like, do read, you kinky son-of-a-bitch!!!</p>
            </blockquote>





	Last Chance at a First Time

**Author's Note:**

  * Translation into 中文 available: [Last Chance at a First Time](https://archiveofourown.org/works/3545780) by [La_Perdition](https://archiveofourown.org/users/La_Perdition/pseuds/La_Perdition)



Only one man knew about Dean's feelings for Sam and that was Dean. Over the years, Dean had denied it, said it was impossible and even tried to drink it away, but finally he had given up and let his desire simmer ravenously inside him.  
It wasn't until Sam started the trials, that Dean realized he may lose his brother again and he decided to act on his feelings. It started out as little things. A hand on Sam's shoulder in the morning; sitting next to Sam, instead of opposite and giving little sideways smiles and glances.  
Then slowly it became, a hand run through Sam's hair or a stroke of the arm, or even a playful kiss on the cheek before bed and to Dean's surprise, Sam never questioned his actions. Never objected to be touched so by Dean.

Then one night, Dean decided to test his boundaries more than usual. Sam had been in bed for about twenty minutes and Dean opened the bedroom door quietly. The room was dark, but the light from the hall, illuminated the bed, where Sammy lay, on his side, facing away from the door. The covers were down to his waist and his bare back rippled with muscle as he breathed, and made Dean swallow, hard.  
Dean was only wearing sweatpants, with nothing underneath and the more he though about Sam, lying there, virtually naked...the more he noticed the blood flowing away from his 'upstairs brain'.

Dean approached the bed carefully, treading lightly, so as not to wake Sam. He lay down on the bed, conscious of every movement, every rustle, every breath. Sam stirred slightly, sighing quietly and muttering some indistinguishable words.  
Dean lay facing his brother's back,about half a meter away. He stared through the darkness at Sammy's gleaming skin, just enjoying the closeness. Suddenly, Sam's deep breathing stop, he was breathing normally and the relaxed appearance of sleep left his muscles. He was awake.

Dean lay very still, not sure what to do. How would Sam react? What would he say? Slowly Sam turned over, the bed sheets shifting down his hips, giving Dean a tantalizing view of his delicious man-hips. Much to Dean's surprise, Sam smiled and moved closer to Dean so their noses were only centimeters away.

"Come to tuck me in?" He asked innocently and Dean gulped, still unsure of his position. Slowly he shook his head.  
"Good," whispered Sam, "Because I am not ready to sleep."  
Dean closed his eyes and took a deep breath, hoping against hope Sam was thinking along the same lines he was and then he reached out and put his palm on Sammy's cheek. Sam reached up and covered Dean's hand with his own, smiling slightly. Dean leaned in and brushed his lips, softly against Sam's. Sam moaned quietly and closed his eyes as Dean ran his tongue over his little brother's bottom lip.

Encouraged, Dean pressed his lips to Sam's with greater force, raising himself onto his elbow next to Sam, so he was leaning over his brother. Sam kissed back passionately, wrapping his arms around Dean's neck and pulling him even closer. After that, Dean lost all pretense and began to grind his erection into Sam's hip, Sam moaned again and tried to pull Dean on top of him. Dean obliged and slid between his brothers legs, grinding their pelvis' together.

Sam was only wearing low cut boxer briefs and Dean, his sweatpants (with nothing underneath), but Dean felt a loathing towards the fabric that kept he and Sam apart. He broke of kissing Sam and knelt between his legs, looking him in the eyes hungrily, slowly he removed Sam's briefs and threw them aside, before taking in the beautiful view. Sam was huge and Dean licked his licks hungrily, before lying back down on his brother's chest, determined to take his time, enjoying Sammy's delicious body.

"Your turn," Sam said huskily, biting Dean's neck gently and sending shivers of pleasure straight to Dean's aching cock. Sam took Dean's hips and turned them both over so he was straddling him. Sam began to touch himself slowly and then he started to stroke Dean through the fabric of his sweats. Dean could feel the precum leaking out all over his shaft and down his balls as he watched Sammy work. The younger Winchester had leaned his head back and hand his eyes closed as he took both his hands and started to remove Dean pants. He hooked his thumbs in the waistband and dragged them down slowly, now watching as Dean's hard-on sprang free from it's mediocre confines.  
Sam wrapped his fingers around Dean's cock and squeezed, ever so slightly. Dean bit his lip and grabbed Sam's arms, pulling the larger man down on top of him and resuming the kiss. This time it was a kiss that engulfed them body and soul, it had never felt so right as they ground their nakedness against each other.

Dean held his huge brother's biceps, digging his nails in possessively. Sammy held the sides of Dean's head and kissed him fiercely. After allowing his brother control for a few minutes, Dean decided to take the wheel. He pushed Sam of him and rolled him over. Sam willingly relinquished control to his big brother and lay obediently on his back, arms stretched above his head and his hands grasping the head of the bed.

Slowly, Dean climbed between Sam's legs, spreading them as he did. He cupped Sam's balls in one hand and massaged them gently. Sam bit his lip and tried to breath deeply, but what Dean did next was almost to much. Dean reached out his other hand and slipped one...then two fingers into Sammy's mouth. Sam suck them moaning quickly his hips rising at Dean's touch. Dean watched his brother pretending the fingers were a cock and growled with longing, massaging Sam's balls harder.

Eventually he removed hos fingers from Sam's mouth. They were dripping with saliva and Dean gently began to work one of them into Sam's anus. Sam tensed and grimaced in pain. It hurt more than he had thought, but when Dean stopped and looked him worriedly in the eye, Sam gritted his teeth and nodded. He wanted to feel Dean inside him, no matter the pain he had to endure.

"Just relax, Sammy," Dean whispered, "It'll hurt a lot less if you relax."

Sam took a deep breath and forced himself to relax. Almost immediately the pain ceased and Dean finger began to slip in and out of him with ease. The sensation was unfamiliar, but not unpleasant and when Dean reached deeper and found that little circle of muscle, Sam gasped in pleasure and looked at Dean in obvious surprise. Dean smiled and slowly put eased another finger inside his brother, joining the first finger, as they ticked his prostate.

Sam's cock was throbbing and his whole abdomen was ablaze with lustful fire he was struggling for control over his actions, the only ting keeping him grounded was his grip on the bed head. Dean began to move his fingers in and out of Sam's ass, finger fucking him faster and faster, until Sam was panting with need, because each time the fingers entered, they just barely brushed his sweet spot and Sammy knew how much better it would feel if he was being pounded into with Dean's enormous manhood.

"Dean, please. Please!" He begged, breathing heavily his arms shaking as he struggled to remain holding the bed head.

"What, Sammy?" Dean asked smirking, knowing full well, and continuing to fuck Sam with his fingers. "What do you want?"

"Dean, you fucking...know...exactly...what..." Sam gasped his eyes closed and his hips attempting to thrust onto Dean's fingers.

"Your right! I do, know. But, I want to hear you say it." Dean admitted, stroking Sam's thigh gently with his free hand and ceasing his other movements, but leaving his fingers inside Sam.

"I want your cock inside me, big brother." Sam said quietly, "I want you to fuck me so hard I see stars."

"Whore!" Dean whispered and Sam grinned up at him, putting his knees on Dean's shoulders.

"Only for you." He said back as he watched Dean moistened his cock with his own saliva this time and place the head of the delicious enormity at his entrance.

"You ready, Sammy?" Dean asked and Sam nodded. "Ok." said Dean, and began to work his throbbing length into Sammy's tight, hot ass.

Dean slid his throbbing cock into Sammy's ass, little by little. Feeling it tightened around him, it was the greatest thing he had ever felt. Being with women had felt different. Good. But, different and being with Sammy just felt perfect, even though it was wrong. But, Dean wanted more. He thrust it inside, deeper and deeper each time, until he was pounding his thighs against Sam's sweet ass. Sam was flinching each time but he was moaning too, clearly enjoying it, even with the pain.

Dean put my hands on Sam's legs for a better hold, so he could thrust faster and faster. The pressure was building Dean was so aroused he couldn't hold it in anymore. With a loud satisfied grunt he came, Dean came inside Sammy's ass. Sam moaned deeply, jerking his own cock feverishly as more cum flooded out of Dean. They were both breathing heavily now, but Dean was not nearly done with Sammy's body yet.

Sam was still rock hard and was desperately stroking himself, eyes closed, aroused beyond belief. Dean pulled out and let Sam's legs fall to the bed, before leaning forward and kissed Sam's mouth before moving slowly downwards.

"I am not letting this go to waste." He murmured between kisses and Sam just mewled in agreement and grabbed Dean's hair with one hand, pushing him further down.

Dean slid down Sam's body stopping on the way to feel rock hard nipple against his face, Dean approached Sam's crotch and put hand around it, it was warm to his touch. Dean blew against Sammy's balls, taking it all in, as he slowly stroked the magnificent beast. He looked up and over to see Sam looking down at him, Dean's eyes were fixed on Sam's as he hovered over with his mouth open. Sam's balls were firmly in Dean's hand now, his cock almost penis wriggling at the excitement of what he knew Dean was about to do. Dean gently licked up the tip to then wrap his mouth around Sam's dick. Sam let out a long husky moan, with every stroke, every suck Dean did, his breath became heavier and heavier. Dean was pumping up and down in gentle rhythm with his hand and mouth together. Then Dean started to feel Sam's balls tighten, he was getting more and more excited. Dean moved his face away and began pumping furiously now.

"Holy fuck, Dean!" Sammy yelled as Dean licked up the side, before taking Sammy's entire cock into his mouth to finish. Sam moaned and cum came shooting out, down Dean's throat and he swallowed every drop.

Once they had gotten cleaned up, Dean and Sam returned to Sam's bed and lay together in the dark, just holding each other close. Dean had his arm over Sammy's stomach and his head on his chest. Dean was almost asleep, when Sam whispered.

"We should do this again sometime."

Dean chuckled and breathed in Sam's warm smell.

"Let me take a quick nap and we CAN do it again." he whispered back. Sam ran his fingers through Dean's hair and lifted his head to kiss him.

"It had better be a VERY quick nap then."

"Don't worry, it will be."


End file.
